Organic compound and application thereof, and organic electroluminescent device containing organic compound

Abstract

The invention relates to an organic compound containing boron and nitrogen, belongs to the technical field of organic light-emitting materials, and also relates to application of the compound in an organic light-emitting device. The organic compound has a structure as shown in the following formula. The organic compound provided by the invention is low in triplet state energy level, so that the stability is better, and a device prepared from the compound shows higher efficiency and longer service life. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a boron-nitrogen-containing organic compound, belonging to the technical field of organic light-emitting materials. The present invention also relates to the application of the compound in an organic electroluminescent device. Background Art

[0002] With the continuous progress and development of social sciences, display technology has become crucial in people's lives. Organic electroluminescent diodes (OLEDs) have become one of the current mainstream display devices due to their many advantages such as flexibility, bendability, self-luminescence, high contrast, large size, and low power consumption.

[0003] The light-emitting mechanism of OLEDs is that electrons and holes recombine to form excitons under electrical excitation. The excitons follow a probability statistical distribution, with singlet excitons accounting for approximately 25% and triplet excitons accounting for approximately 75%. The first-generation light-emitting technology is collectively referred to as fluorescence technology, which uses singlet excitons to emit light; the second-generation light-emitting technology is collectively referred to as phosphorescence technology, which uses triplet excitons to emit light. In theory, 100% internal quantum efficiency can be achieved. However, the heavy metals required to construct phosphorescent dyes are not only expensive but also pollute the environment. Therefore, the currently commonly used third-generation thermally activated delayed fluorescence technology constructed with organic small molecules is adopted. When the singlet-triplet energy level difference is very small, triplet excitons can undergo reverse intersystem crossing to the singlet state and then return to the ground state to emit light. Among them, the red and green dyes as the three primary colors have become the mainstream of current commercial display devices due to their high electroluminescence efficiency and low power consumption. However, the chromaticity and lifespan of blue light materials do not meet the current commercial display requirements, and blue light devices still use traditional fluorescent materials to achieve high color purity and long device lifespan.

[0004] In recent years, research groups such as Takuji Hatakeyama and Junji Kido in Japan have reported a series of organic small molecule materials DABNA-1 based on boron-nitrogen resonance-type thermally activated delayed fluorescence (Adv. Mater. 2016, 28, 2777–2781; J. Mater. Chem. C, 2019, 7, 3082-3089). In these compounds, boron atoms, nitrogen atoms, and phenyl groups form a rigid polycyclic aromatic resonance skeleton, thus having a high fluorescence quantum yield. Compared with traditional blue fluorescent dyes, these compounds have a narrower emission spectral bandgap and higher color purity. However, the rigid planar structure also leads to a large energy level difference between the singlet and triplet states, slow reverse intersystem crossing from the triplet state to the singlet state, and serious efficiency roll-off after excitons recombine on the dye, resulting in a short device lifespan. In addition, the overly planar rigid structure often also causes adverse effects such as broadening and red shift of the emission spectrum due to too high doping concentration.

[0005]

[0006] Existing organic electroluminescent materials still have great room for improvement in terms of luminescence performance. The industry urgently needs to develop new luminescent material systems to meet commercial requirements. Boron-nitrogen resonance materials have the advantages of high color purity and high luminescence efficiency, which have attracted extensive attention in the scientific research community and the industrial community. However, due to the small influence of peripheral substituents on their energy levels, that is, it is difficult to regulate the luminescence color of the materials, and their light colors have been limited to the sky blue region, which greatly restricts the further application of such materials in the fields of high-resolution display, full-color display, and white light illumination.

[0007] As OLED products gradually enter the market, people have higher and higher requirements for the performance of such products. The currently used OLED materials and device structures cannot completely solve various problems such as efficiency, lifespan, and cost of OLED products. The researchers of the present invention, through careful thinking and continuous experiments, discovered a clever molecular design scheme, which will be described in detail below. Surprisingly, the compounds disclosed in the present invention are very suitable for application in OLEDs and can improve the device lifespan. Summary of the Invention

[0008] The present invention designs a class of resonance fluorescent dyes containing boron-nitrogen structures that can emit deep blue light, and can effectively improve device efficiency and lifespan.

[0009] The present invention provides a boron-nitrogen-containing organic compound having a structure represented by the general formula (1):

[0010]

[0011] In formula (1), ring A, ring D, and ring E are each independently one of a C6-C50 aromatic ring and a C3-C50 heteroaromatic ring;

[0012] Ra, Rd, and Re represent substituents from single substitution to the maximum allowable number of substituents, and Ra, Rd, and Re are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.

[0013] Ar1 and Ar2 are each independently one of an unsubstituted or R'-substituted C6-C50 aryl group or an unsubstituted or R'-substituted C3-C50 heteroaryl group;

[0014] Adjacent R's are not connected or are connected by a chemical bond to form a ring; the R' is not connected to an adjacent ring structure or is connected by a chemical bond to form a ring;

[0015] Moreover, at least one of Ra, Rd, Re, Ar1, and Ar2 is selected from the structures shown in formula (2) or formula (3);

[0016]

[0017] In formula (2) and formula (3), L1 is selected from a single bond, an unsubstituted or R''-substituted C1-C20 linear alkyl group, or an unsubstituted or R''-substituted C6-C60 aryl group;

[0018] X1, X2, X3, X4, X5, X6, X7, X8, X9, X 10 , X 11 , X 12 are each independently N or CR 11 , R 11 are each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, an unsubstituted or R''-substituted C1-C20 linear alkyl group, an unsubstituted or R''-substituted C3-C20 cycloalkyl group, an unsubstituted or R''-substituted C6-C30 arylamino group, an unsubstituted or R''-substituted C3-C30 heteroarylamino group, an unsubstituted or R''-substituted C6-C60 aryl group, or an unsubstituted or R''-substituted C3-C60 heteroaryl group;

[0019] R 11 are each independently not connected to an adjacent ring structure;

[0020] "*" represents a connection site; the expression of a ring structure with a "-" drawn through it indicates that the connection site is at any position on the ring structure where a bond can be formed;

[0021] R' and R'' are each independently selected from halogen, cyano, nitro, hydroxy, amino, a C1-C20 linear alkyl group, a C2-C20 alkenyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C1-C20 alkylamino group, a C6-C60 arylamino group, a C3-C60 heteroarylamino group, a C6-C30 aryloxy group, a C3-C30 heteroaryloxy group, a C6-C60 aryl group, or a C3-C60 heteroaryl group, or any combination of at least two of them.

[0022] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning, and the selection range of the substituents is as shown above and will not be elaborated one by one.

[0023] In this specification, the expression "Ca - Cb" represents that the group has a carbon atom number of a - b. Generally, unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

[0024] In this specification, the expression of a ring structure with a "-" drawn across it indicates that the connection site is at any bond-forming position on the ring structure.

[0025] In this specification, "independently of each other" means that when the subject has multiple entities, they may be the same or different from each other.

[0026] In the present invention, for the expression of chemical elements, unless otherwise specified, it usually includes the concept of its isotopes. For example, the expression "hydrogen (H)" includes the concepts of its isotopes 1H (protium or H), 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., and will not be elaborated further.

[0027] The heteroatoms in the present invention usually refer to atoms or atomic groups selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S.

[0028] In this specification, examples of halogens include: fluorine, chlorine, bromine, iodine, etc.

[0029] In the present invention, unless otherwise specified, aryl and heteroaryl both include monocyclic and fused-ring cases.

[0030] In the present invention, the C6 - C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

[0031] The C3 - C60 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

[0032] Any of C1-C20 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, etc.

[0033] Any of C3-C20 may be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, etc.

[0034] Any of C6-C30 may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.

[0035] Any of C3-C30 may be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.

[0036] Any of C2-C10 may be C2, C3, C4, C5, C6, C7, C8, C9, or C10.

[0037] In the present invention, the substituted or unsubstituted C6-C60 aryl group (or C6-C50 aryl group) includes monocyclic aryl groups and fused-ring aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. The so-called monocyclic aryl group means a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are connected by single bonds. Exemplarily, such as: phenyl, biphenyl, terphenyl, etc. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl. The fused-ring aryl group means a group in which the molecule contains at least two aromatic rings, and the aromatic rings are not independent of each other but are fused to each other by sharing two adjacent carbon atoms. Exemplarily, such as: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, Groups such as a base, a tetracenyl group, and their derivative groups. The naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthryl group is selected from a 1-anthryl group, a 2-anthryl group, and a 9-anthryl group; the fluorenyl group is selected from a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group; the pyrenyl group is selected from a 1-pyrenyl group, a 2-pyrenyl group, and a 4-pyrenyl group; the tetracenyl group is selected from a 1-tetracenyl group, a 2-tetracenyl group, and a 9-tetracenyl group. The derivative group of fluorene is selected from a 9,9-dimethylfluorenyl group, a 9,9-diethylfluorenyl group, a 9,9-dipropylfluorenyl group, a 9,9-dibutylfluorenyl group, a 9,9-dipentylfluorenyl group, a 9,9-dihexylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9,9-dinaphthylfluorenyl group, a 9,9'-spirobifluorenyl group, and a benzofluorenyl group.

[0038] The C3-C60 heteroaryl group (or C6-C50 heteroaryl group) mentioned in the present invention includes a monocyclic heteroaryl group and a polycyclic heteroaryl group, preferably a C3-C30 heteroaryl group, further preferably a C4-C20 heteroaryl group, and more preferably a C5-C12 heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as an aryl group, a heteroaryl group, an alkyl group, etc.), the heteroaryl group and other groups are independent of each other and are connected by a single bond. Examples of the monocyclic heteroaryl group include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, etc. The polycyclic heteroaryl group means that the molecule contains at least one heteroaromatic ring and an aromatic ring (heteroaromatic ring or aryl ring), and the two are not independent of each other but are fused with each other by sharing two adjacent atoms. Examples of the polycyclic heteroaryl group include a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an acridinyl group, an isobenzofuryl group, an isobenzothienyl group, a benzocarbazolyl group, an azacarbazolyl group, a phenothiazinyl group, a phenazinyl group, a 9-phenylcarbazolyl group, a 9-naphthylcarbazolyl group, a dibenzocarbazolyl group, an indolocarbazolyl group, etc.

[0039] Specific examples of the arylene group in the present invention can be a divalent group obtained by removing one hydrogen atom from the examples of the above aryl groups. The number of carbon atoms in the arylene group includes but is not limited to C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. Specific examples of the heteroarylene group in the present invention can be a divalent group obtained by removing one hydrogen atom from the examples of the above heteroaryl groups.

[0040] The aryloxy group or heteroaryloxy group in the present invention can be a monovalent group formed by an oxygen atom and the above aryl group or heteroaryl group.

[0041] In the present invention, the arylamino group represents a group formed by replacing one or two hydrogen atoms on the substituted amino group with an aryl group, wherein the connection site of the arylamino group can be connected to the aryl group in the arylamino group or to the N in the arylamino group, and the exemplary number of carbon atoms and specific groups of the aryl group in the arylamino group are the same as those above.

[0042] The C6-C30 arylamines mentioned in the present invention include, for example: phenylamine, methylphenylamine, naphthylamine, anthrylamine, phenanthrylamine, biphenylamine, etc.

[0043] The C3-C30 heteroarylamines mentioned in the present invention include, for example: pyridylamine, pyrimidinylamine, dibenzofuranyl amine, etc.

[0044] In the present invention, the linear alkyl groups mentioned, unless otherwise specified, include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, the substituted or unsubstituted C1-C20 linear alkyl groups are preferably substituted or unsubstituted C1-C16 linear alkyl groups, and more preferably substituted or unsubstituted C1-C10 linear alkyl groups. Examples of the substituted or unsubstituted C1-C10 linear alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0045] In the present invention, the cycloalkyl groups include monocyclic alkyl groups and polycyclic alkyl groups; among them, the monocyclic alkyl group refers to an alkyl group containing a single cyclic structure; the polycyclic alkyl group refers to a structure formed by two or more cycloalkyl groups sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0046] In this specification, as the substituted or unsubstituted C1-C20 alkoxy group, preferably the substituted or unsubstituted C1-C10 alkoxy group, examples of the C1-C20 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are preferred, and methoxy is more preferred.

[0047] In this specification, as the substituted or unsubstituted C1-C20 silyl group, as the substituted or unsubstituted C1-C10 silyl group, examples of the C1-C10 silyl group can be silyl groups substituted by the groups exemplified in the above C1-C10 linear alkyl groups, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and other groups.

[0048] In the present specification, the C2-C20 alkenyl group, preferably the C2-C10 alkenyl group, is a hydrocarbon group containing at least one C=C double bond, and illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0049] It should be noted that, while the potential effects of various groups / features are described separately for ease of explanation, this does not imply that these groups / features function in isolation. In fact, the key to achieving good performance is the optimized combination of the entire molecule, resulting from the synergistic effects of the various groups, rather than the effects of any single group.

[0050] Furthermore, in the boron-nitrogen-containing organic compound of the present invention, the ring E has a structure as shown in formula (c):

[0051]

[0052] Among them, the dotted line represents the fused bond of the group;

[0053] Z 1 、Z 2 , Z 3 Each independently CR 12 or N;

[0054] R 12 Each is independently selected from at least one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl; adjacent R 12 They are not connected or connected to form a ring through chemical bonds; R 12 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond;

[0055] Preferably, the Z 1 、Z 2 、Z 3 At most one of them is N.

[0056] Furthermore, the boron-nitrogen-containing organic compound involved in the present invention has a structure as shown in formula (1-1):

[0057]

[0058] In formula (1-1), Z 1 、Z 2 、Z 3 Having the same definition as in formula (c);

[0059] Ring A, Ring D, Ar1, Ar2, R a , R d has the same defined range as in formula (1);

[0060] Preferably, in formula (1-1), the Z 1 , Z 2 , Z 3 at most one of them is N;

[0061] Preferably, in formula (1-1), the Z 1 , Z 2 , Z 3 are each independently CR 12 .

[0062] Furthermore, for the boron-nitrogen-containing organic compound involved in the present invention, Ring A and Ring D have the structures shown in formula (d) or formula (e):

[0063]

[0064] wherein, the dashed line represents the fused bond of the group;

[0065] X is selected from O or S;

[0066] U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 are each independently CR 13 or N;

[0067] R 13 are each independently selected from at least one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl;

[0068] Adjacent R 13 are not connected or are connected by a chemical bond to form a ring; R 13 are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring;

[0069] Preferably, the U 1 , U 2 , U 3 and U 4 at most one of them is N; the U 5 , U6 , U 7 and U 8 At most one of them is N;

[0070] Preferably, the U 1 , U 2 , U 3 and U 4 are each independently CR 13 ; the U 5 , U 6 , U 7 and U 8 are each independently CR 13 .

[0071] Furthermore, for the boron-nitrogen-containing organic compound involved in the present invention, the boron-nitrogen-containing organic compound has a structure shown in Formula (3-1) or Formula (3-2):

[0072]

[0073] wherein X has the same defined range as in Formula (e);

[0074] U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 have the same defined ranges as in Formulas (d) and (e);

[0075] U 1 ', U 2 ', U 3 ', U 4 ' are defined in the same range as U 1 , U 2 , U 3 , U 4 ;

[0076] Z 1 , Z 2 , Z 3 have the same defined range as in Formula (c);

[0077] Ar1 and Ar2 have the same defined ranges as in Formula (1).

[0078] Preferably, the boron-nitrogen-containing organic compound has a structure shown in Formula (3-1).

[0079] Continuing preferably, in the above general formula, the Z 1 , Z 2, Z 3 Each independently is CR 12 , U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 1 ', U 2 ', U 3 ', U 4 ' Each independently is CR 13 ;

[0080] The said R 12 , R 13 , Ar1, Ar2 at least one of which is selected from the structures shown in formula (2) or formula (3).

[0081] Preferably, at least one of Ar1, Ar2 is selected from the structures shown in formula (2) or formula (3).

[0082] Preferably, one of Ar1, Ar2 is selected from the structures shown in formula (2) or formula (3), and the other is selected from one of unsubstituted or R'-substituted C6-C30 aryl, unsubstituted or R'-substituted C3-C30 heteroaryl, R' is selected from one or at least two combinations of C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C30 arylamino, C6-C30 aryloxy, C6-C30 aryl, C3-C30 heteroaryl, for example the other is selected from one of the following groups:

[0083]

[0084] "*" represents the connection site; the expression of the ring structure crossed by "-" indicates that the connection site is at any bond-forming position on the ring structure.

[0085] Preferably, the said at least one R 12 is selected from the structures shown in formula (2) or formula (3).

[0086] For example, the said at least one R 12 is selected from the structures shown in formula (2) or formula (3), and the remaining Rs 12 each independently is selected from one or two combinations of hydrogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C3-C60 heteroaryl.

[0087] Ar1 and Ar2 are each independently selected from an unsubstituted or R'-substituted C6-C30 aryl group or an unsubstituted or R'-substituted C3-C30 heteroaryl group, and R' is selected from a C1-C10 linear alkyl group, a C3-C10 cycloalkyl group, a C6-C30 arylamino group, a C6-C30 aryloxy group, a C6-C30 aryl group, a C3-C30 heteroaryl group, or a combination of at least two of them. For example, Ar1 and Ar2 are each independently selected from the following groups:

[0088]

[0089] etc. "*" represents the connection site; the expression of the ring structure with a "-" drawn across it means that the connection site is at any position on the ring structure where bonding can occur.

[0090] More preferably, in formulas (2) and (3), the X1-X 12 are each independently CR 11 , and the R 11 are each independently selected from hydrogen, an unsubstituted or R''-substituted C1-C20 linear alkyl group, an unsubstituted or R''-substituted C3-C20 cycloalkyl group, an unsubstituted or R''-substituted C6-C30 arylamino group, an unsubstituted or R''-substituted C3-C30 heteroarylamino group, an unsubstituted or R''-substituted C6-C60 aryl group, an unsubstituted or R''-substituted C3-C60 heteroaryl group. Preferably, at least one R 11 is selected from hydrogen, an unsubstituted or R''-substituted C1-C20 linear alkyl group, an unsubstituted or R''-substituted C6-C60 aryl group, an unsubstituted or R''-substituted C3-C60 heteroaryl group;

[0091] The R'' are each independently selected from a halogen, a cyano group, a C1-C20 linear alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C1-C20 alkylamino group, a C6-C60 arylamino group, a C3-C60 heteroarylamino group, a C6-C30 aryloxy group, a C3-C30 heteroaryloxy group, a C6-C60 aryl group, a C3-C60 heteroaryl group, or a combination of at least two of them;

[0092] Preferably, in formulas (2) and (3), the X1-X 12 are each independently CR 11 , and the R 11 are each independently selected from hydrogen, an unsubstituted or R''-substituted C1-C20 linear alkyl group, an unsubstituted or R''-substituted C3-C20 cycloalkyl group, an unsubstituted or R''-substituted C6-C60 aryl group, an unsubstituted or R''-substituted C3-C60 heteroaryl group. Preferably, at least one R 11Selected from one of hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl;

[0093] Each of the R”s is independently selected from one or a combination of two of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl;

[0094] More preferably, in formula (2) and formula (3), the X1-X 12 are each independently CR 11 , and the Rs 11 are each independently selected from one of hydrogen, unsubstituted or R”-substituted C1-C10 linear alkyl, unsubstituted or R”-substituted C3-C10 cycloalkyl, unsubstituted or R”-substituted C6-C30 aryl, and unsubstituted or R”-substituted C3-C30 heteroaryl. Preferably, at least one R 11 is selected from one of hydrogen, unsubstituted or R”-substituted C1-C10 linear alkyl, unsubstituted or R”-substituted C6-C30 aryl, and unsubstituted or R”-substituted C3-C30 heteroaryl;

[0095] Each of the R”s is independently selected from one or a combination of two of C1-C6 linear alkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0096] For example, at least one R 11 is selected from at least one of hydrogen, methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, phenyl, naphthyl, and pyridyl.

[0097] Furthermore, in formula (2) and formula (3), L1 is connected to X1 or X2; preferably, L1 is selected from one of a single bond, unsubstituted or R”-substituted C6-C20 aryl, and each of the R”s is independently selected from one or a combination of two of C1-C6 linear alkyl, C6-C20 aryl, and C3-C20 heteroaryl; for example, L1 is selected from one of a single bond, phenyl, methylphenyl, tert-butylphenyl, and naphthyl.

[0098] Preferably, in formula (2), X7 is CR 11 , where this R 11 is selected from one of hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl; each of the R”s is independently selected from one of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl; more preferably, in formula (2), X7 is CR 11 , where this R 11Selected from one of hydrogen, C1-C20 linear alkyl, C6-C60 aryl, and C3-C60 heteroaryl, X1 to X6, X8 to X 12 are each independently CR 11 , R 11 is selected from hydrogen. More preferably, in formula (2), X7 is CR 11 , where this R 11 is selected from one of hydrogen, C1-C10 linear alkyl, C6-C20 aryl, and C3-C20 heteroaryl. Further preferably, X7 is CR 11 , where this R 11 is selected from one of hydrogen, C6-C20 aryl, and C3-C20 heteroaryl; X1 to X6, X8 to X 12 are each independently CR 11 , R 11 is selected from hydrogen.

[0099] Preferably, in formula (3), X5, X6, X9, X 10 are each independently CR 11 , where R 11 are each independently selected from one of hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl; the said R” are each independently selected from one of C1-Cio linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl; More preferably, in formula (3), X5, X6, X9, X 10 is CR 11 , where R 11 are each independently selected from one of hydrogen, C1-C20 linear alkyl, C6-C60 aryl, and C3-C60 heteroaryl, X1 to X4, X7 to X8, X 11 to X 12 are each independently CR 11 , R 11 is selected from hydrogen. More preferably, in formula (3), X5, X6, X9, X 10 is CR 11 , where R 11 are each independently selected from one of hydrogen, C1-C10 linear alkyl, C6-C20 aryl, and C3-C20 heteroaryl. Further preferably, X5, X6, X9, X 10 is CR 11 , where R 11 are each independently selected from one of hydrogen, C6-C20 aryl, and C3-C20 heteroaryl; X1 to X4, X7 to X8, X 11 to X 12 are each independently CR 11 , R11 Selected from hydrogen.

[0100] Continuing further, in the above general formula, the R 12 , R 13 At least one of them is selected from the structures shown in formula (2) or formula (3), and the remaining R 12 , R 13 Are each independently selected from one or a combination of two of hydrogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, and C3-C60 heteroaryl; or R 12 , R 13 Are each independently selected from one or a combination of two of hydrogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, and C3-C60 heteroaryl;

[0101] Preferably, at least one of the R 12 , R 13 Is selected from the structures shown in formula (2) or formula (3), and the remaining R 12 , R 13 Are each independently selected from one or a combination of two of hydrogen, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C20 arylamino, C6-C20 aryl, and C3-C20 heteroaryl; or R 12 , R 13 Are each independently selected from one or a combination of two of hydrogen, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C20 arylamino, C6-C20 aryl, and C3-C20 heteroaryl.

[0102] For example, at least one R 12 Or at least one R 13 Is selected from the structures shown in formula (2) or formula (3), and the remaining R 12 , R 13 Are each independently selected from one of hydrogen, methyl or the following groups, or R 12 , R 13 Are each independently selected from one of hydrogen, methyl or the following groups:

[0103] etc.

[0104] Furthermore, the organic compounds of the present invention can preferably select the specific structural compounds M1 to M76 shown below. These compounds are only representative and do not limit the scope of the present invention:

[0105]

[0106]

[0107]

[0108]

[0109] The preparation process of the compounds of the present invention is simple and easy to implement, and the raw materials are readily available, suitable for mass production scale-up, and very suitable for industrial applications.

[0110] The present invention uses a boron atom and two N atoms to form a multiple resonance mother nucleus with a benzene ring. Due to the strong electron-withdrawing and electron-donating effects of the B atom and N atom, this structure can achieve excellent multiple resonance effects, effectively narrowing the emission spectrum of the compound. And by introducing substituted or unsubstituted benzoanthracene or substituted or unsubstituted helicene groups at the para position of the B atom or on the N atom, the energy level of the triplet state (T1 state) of the compound is effectively reduced, the energy released by exciton quenching is reduced, and material cleavage is prevented, thereby improving the lifetime and efficiency of the device.

[0111] As another aspect of the present invention, there is also provided an application of the above-mentioned compound in an organic electroluminescent device. Specifically, the above-mentioned compound of the present invention has excellent luminescence properties, can give triplet excitons to achieve a high luminescence efficiency, and at the same time, based on its excellent carrier transport efficiency, it is suitable for use as a luminescent dye.

[0112] Of course, since the compounds of the present invention can also be used as sensitizers to achieve a good light-emitting layer together with the host material and the dye. The devices to which it is applied include, but are not limited to, organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic papers, preferably organic electroluminescent devices.

[0113] The present invention also provides an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one or more light-emitting functional layers inserted between the first electrode and the second electrode, and at least one of the compounds of the present invention is contained in the light-emitting functional layer.

[0114] The structure of the organic electroluminescent device of the present invention is consistent with the existing devices. For example, it includes an anode layer, a plurality of light-emitting functional layers, and a cathode layer; the plurality of light-emitting functional layers include an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the above-mentioned organic compound of the present invention is contained in the light-emitting layer.

[0115] Preferably, the light-emitting layer further includes a host material, and the host material has a structure represented by the general formula (a) or formula (b):

[0116]

[0117] In formulas (a) and (b), L 11 , L 12 is each independently one of a single bond, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group;

[0118] Ar 11 , Ar 12 , Ar 21 , Ar 22 is each independently one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;

[0119] n represents any integer from 0 to 3 (for example, 0, 1, 2, 3);

[0120] The above-mentioned substituting groups are each independently any one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C2O linear alkyl, C2-C2O alkenyl, C3-C2O cycloalkyl, C1-C2O alkoxy, C6-C3O aryl, and C3-C3O heteroaryl.

[0121] More preferably, L 11 , L 12 is each independently a single bond, phenyl, naphthyl, dibenzothiophene, dibenzofuran, or 9,9-dimethylfluorenyl.

[0122] More preferably, Ar 11 , Ar 12 , Ar 21 , Ar 22 is each independently selected from one of the following substituted or unsubstituted groups:

[0123]

[0124] Ar 11 , Ar 12 , Ar 21 , Ar 22 The substituting groups in are each independently selected from any one or a combination of at least two of halogen, cyano, C1-C10 linear alkyl, C6-C30 aryl, and C3-C30 heteroaryl, and are further preferably any one of C1-C6 linear alkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0125] Preferably, the host material has a structure represented by general formula (a).

[0126] Furthermore, the main material of the present invention can preferably be the following specific structural compounds BFH-1 to BFH-21. These compounds are only representative (the main material can be prepared by the methods disclosed in the prior art), and do not limit the scope of the present invention:

[0127]

[0128] The OLED device prepared with the compound of the present invention has a low turn-on voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturing enterprises for high-performance materials. Detailed implementation manners

[0129] Synthesis Example 1

[0130] Synthesis of Compound M1

[0131]

[0132] Synthesis of Intermediate M1-1:

[0133] Add 50 g of 5-bromo-1,3-diiodobenzene, 68.85 g of bis(4-tert-butylphenyl)amine, 23.29 g of copper(I) iodide, 44.08 g of 1,10-phenanthroline, and 51.92 g of potassium phosphate into a 2000 mL flask, add 500 mL of DMF, heat to reflux under nitrogen protection for 15 hours, evaporate the solvent, mix with silica gel and perform column chromatography to obtain 71.6 g of a white solid. The molecular weight detected by mass spectrometry is 714.71 (theoretical value 714.86).

[0134] Synthesis of Intermediate M1-2:

[0135] Add 50 g of Intermediate M1-1, 19.1 g of 9-boronic acid-[3,4]benzanthracene, 4.04 g of tetrakis(triphenylphosphine)palladium, and 19.31 g of potassium carbonate into a 2000 mL flask, add 400 mL of 1,4-dioxane and 100 mL of water, heat to reflux under nitrogen protection for 5 hours, evaporate the solvent, mix with silica gel and perform column chromatography to obtain 52.31 g of a white solid. The molecular weight detected by mass spectrometry is 862.39 (theoretical value 862.52).

[0136] Synthesis of Compound M1

[0137] Put 10 g of Intermediate M1-2 into a 500 mL pressure-resistant bottle, add 200 mL of o-dichlorobenzene and 58.04 g of boron tribromide, heat to 180 °C and react for 12 hours, extract with dichloromethane and water, combine the organic phases, evaporate the solvent, mix with silica gel and perform column chromatography to obtain 2.36 g of a yellow solid. The molecular weight detected by mass spectrometry is 870.35 (theoretical value 870.51).

[0138] Synthesis Example 2

[0139] Synthesis of Compound M6

[0140]

[0141] Synthesis of Intermediate M6-1:

[0142] Add 50 g of 5-bromo-1,3-diiodobenzene, 34.5 g of bis(3-tert-butylphenyl)amine, 34.5 g of 3,6-di-tert-butylcarbazole, 23.29 g of copper(I) iodide, 44.08 g of 1,10-phenanthroline, and 51.92 g of potassium phosphate into a 2000 mL flask. Add 500 mL of DMF, heat to reflux under nitrogen protection, react for 15 hours, rotary evaporate the solvent, mix with silica gel and perform column chromatography to obtain 54.3 g of a white solid. The molecular weight detected by mass spectrometry is 712.19 (theoretical value 712.34).

[0143] Synthesis of Intermediate M6-2:

[0144] The synthesis of Intermediate M6-2 is exactly the same as that of Intermediate M1-2, except that M1-1 is replaced with M6-1. The molecular weight detected by mass spectrometry is 860.44 (theoretical value 860.51).

[0145] Synthesis of Compound M6

[0146] The synthesis of Compound M6 is exactly the same as that of Compound M1, except that M1-2 is replaced with M6-2. The molecular weight detected by mass spectrometry is 868.40 (theoretical value 868.49).

[0147] Synthesis Example 3

[0148] Synthesis of Compound M41

[0149]

[0150] Synthesis of Intermediate M41-1:

[0151] Add 50 g of phthalic diboronic acid, [3,4]benzanthrene-9-bromide, 17.43 g of tetrakis(triphenylphosphine)palladium, and 83.38 g of potassium carbonate into a 2000 mL flask. Add 400 mL of 1,4-dioxane and 100 mL of water, heat to reflux, react for 5 hours, stop heating, rotary evaporate the solvent, mix with silica gel and perform column chromatography to obtain 78.05 g of a white solid. The molecular weight detected by mass spectrometry is 348.15 (theoretical value 348.21).

[0152] Synthesis of Intermediate M41-2

[0153] The synthesis of intermediate M41-2 is exactly the same as that of intermediate M1-2, except that 9-boronic acid-[3,4]benzanthracene is replaced with M41-1, and the molecular weight detected by mass spectrometry is 938.45 (theoretical value 938.55).

[0154] Synthesis of compound M41

[0155] The synthesis of M41 is exactly the same as that of M1, except that intermediate M1-2 is replaced with M41-2, and the molecular weight detected by mass spectrometry is 946.41 (theoretical value 946.54).

[0156] The present invention exemplarily provides the specific synthesis methods of the above several compounds. For other compounds without specific synthesis methods, they are also prepared by similar methods, and can be obtained only by replacing the raw materials, which will not be elaborated here, or those skilled in the art can also prepare them by other methods in the prior art.

[0157] Device Embodiment

[0158] Embodiment

[0159] The OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. The organic material can be further divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0160] In a specific embodiment, a substrate can be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, waterproofness, and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate for display use.

[0161] The first electrode can be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof can be used.

[0162] The organic material layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compounds used as the organic material layer can be organic small molecules, organic macromolecules, polymers, and combinations thereof.

[0163] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); where the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0164] The materials of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers, or polymers containing conductive dopants such as poly(phenylene vinylene), polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown by HT-1 to HT-51 below; or any combination thereof.

[0165]

[0166]

[0167]

[0168]

[0169] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can adopt one or more of the above-mentioned compounds of HT-1 to HT-51, or one or more of the following compounds of HI-1 to HI-3; it can also adopt one or more of the compounds of HT-1 to HT-51 doped with one or more of the compounds of HI-1 to HI-3.

[0170]

[0171] The light-emitting layer includes light-emitting dyes (i.e., dopants) that can emit spectra of different wavelengths, and can also include a host material at the same time. The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, or blue. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or stacked together to form a color light-emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0172] According to different technologies, the light-emitting layer material can be a fluorescent electroluminescent material, a phosphorescent electroluminescent material, a thermally activated delayed fluorescence material, or other different materials. In an OLED device, a single light-emitting technology can be adopted, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0173] In one aspect of the present invention, the light-emitting layer adopts the technology of fluorescent electroluminescence. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or a combination of more than one of the above-listed BFH-1 to BFH-21.

[0174] In one aspect of the present invention, the barrier layer around the light-emitting layer can be selected from, but not limited to, one or a combination of more than one of PH-1 to PH-85.

[0175]

[0176]

[0177]

[0178]

[0179] The fluorescent dopant of the light-emitting layer can also be selected from, but not limited to, one or a combination of more than one of the following-listed TDE1-TDE49.

[0180]

[0181]

[0182]

[0183]

[0184] In one aspect of the present invention, the electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer can be made of, but not limited to, one or more compounds of the above-listed HT-1 to HT-51, or made of, but not limited to, one or more compounds of the above-listed PH-47 to PH-77; it can also be made of a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77.

[0185] The OLED organic material layer may further include an electron transport region between the light-emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0186] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or a combination of more than one of ET-1 to ET-73 listed below.

[0187]

[0188]

[0189]

[0190]

[0191] In one aspect of the present invention, the hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may be made of, but not limited to, one or more compounds of ET-1 to ET-73 above, or may be made of, but not limited to, one or more compounds of PH-1 to PH-46; it may also be made of, but not limited to, a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0192] The device may further include an electron injection layer between the electron transport layer and the cathode, and the electron injection layer material includes but is not limited to one or a combination of more than one of the following listed.

[0193] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0194] Device embodiment:

[0195] In this embodiment, the preparation process of the organic electroluminescent device is as follows:

[0196] Manufacturing method of Device Embodiment 1: The glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment until all moisture is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface;

[0197] Place the glass substrate with the anode in a vacuum chamber, evacuate to <1×10 -5Pa, a 10-nm-thick mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum thermally evaporated onto the above-mentioned anode layer film in sequence as the hole injection layer, a 60-nm-thick compound HT-4 as the hole transport layer, a 5-nm-thick compound HT-14 as the electron blocking layer, a 20-nm-thick binary mixture of BFH-4:M1 (100:3, w / w) as the light-emitting layer, a 5-nm-thick ET-23 as the hole blocking layer, a 25-nm-thick mixture of ET-69:ET-57 (50 / 50, w / w) as the electron transport layer, a 1-nm-thick LiF as the electron injection layer, and a 150-nm-thick metallic aluminum as the cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm / second, and the evaporation rate of the metal electrode was controlled at 1 nm / second.

[0198] Device Examples 2 to 14 were fabricated using the same method as Device Example 1, except that the dopants in the light-emitting layer were different. The specific dopant material schemes are shown in Table 1 below.

[0199] Device Comparative Examples 1 to 5 were fabricated using the same method as Device Example 1, except that the dopants in the light-emitting layer were replaced with Compounds C1, C2, C3, C4, and C5 in the prior art, respectively.

[0200]

[0201] Testing methods for the devices (including equipment and test conditions):

[0202] The following performance measurements were performed on the organic electroluminescent devices prepared by the above process:

[0203] The external quantum efficiency (EQE%) of the device was measured using the integrating sphere method;

[0204] At the same brightness, the lifetimes of the organic electroluminescent devices prepared in Examples 1 to 14 and Comparative Examples 1 to 5 were measured using a digital source meter and a PR650. Specifically,

[0205] The LT97 lifetime was tested as follows: Using a luminance meter, the initial luminance value of the device at a current density of 40 mA / cm 2 was measured. Keeping the current constant, the time when the device luminance decreased to 97% of the initial luminance was measured, with the unit of h; taking the LT97 lifetime test value of Device Comparative Example 1 as 1.0, the ratio of the LT97 lifetime test values of other devices to the LT97 lifetime test value of Device Comparative Example 1 was calculated;

[0206] The performance data of the organic electroluminescent devices prepared in the above-mentioned device examples and comparative examples are shown in Table 1 below.

[0207] Table 1:

[0208]

[0209]

[0210] As can be seen from Table 1 above, compared with compounds C1 and C2, the devices prepared with the compounds of the present invention exhibit higher efficiency and longer lifetime. This may be due to the use of a benzoanthracene-based structure or a helicene-based structure in the molecules of the compounds of the present invention. Compared with the group structure used in comparative compounds C1 and C2, the triplet energy level of the compounds of the present invention is lower, so the stability of the compounds is better. At the same time, the larger steric hindrance also enables the compounds of the present invention to effectively inhibit exciton quenching and have higher efficiency.

[0211] Compared with compounds C3 and C4, the devices prepared with the compounds of the present invention have higher efficiency and longer lifetime. This may be because the BO parent nucleus used in compounds C3 and C4 has relatively low luminescence efficiency and poor stability.

[0212] Compared with compound C5, the devices prepared with the compounds of the present invention have higher efficiency and longer lifetime. This may be because the N-heteroxanthene structure in the structure of compound C5 is prone to exciton quenching, thus affecting the luminescence efficiency and stability.

[0213] The specific embodiments described above further elaborate on the objectives, technical solutions, and beneficial effects of the present invention. It should be understood that the above are only specific embodiments of the present invention and are not used to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-nitrogen-containing organic compound, characterized in that, It has a structure shown in General Formula (1): In Formula (1), Ring A, Ring D, and Ring E are each independently one of a C6-C50 aryl ring and a C3-C50 heteroaryl ring; Ra, Rd, and Re represent substituents from single substitution to the maximum allowable number of substituents, and Ra, Rd, and Re are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; Ar1 and Ar2 are each independently one of unsubstituted or R'-substituted C6-C50 aryl and unsubstituted or R'-substituted C3-C50 heteroaryl; Adjacent R's are not connected or are connected by a chemical bond to form a ring; the R' is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; Moreover, at least one of Ra, Rd, Re, Ar1, and Ar2 is selected from the structures shown in Formula (2) or Formula (3); In Formula (2) and Formula (3), L1 is selected from a single bond, unsubstituted or R''-substituted C1-C20 linear alkyl, and unsubstituted or R''-substituted C6-C60 aryl; X1, X2, X3, X4, X5, X6, X7, X8, X9, X 10 、X 11 、X 12 Each independently is N or CR 11 , R 11 Each is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R″-substituted C1-C20 chain alkyl, unsubstituted or R″-substituted C3-C20 cycloalkyl, unsubstituted or R″-substituted C6-C30 arylamino, unsubstituted or R″-substituted C3-C30 heteroarylamino, unsubstituted or R″-substituted C6-C60 aryl, and unsubstituted or R″-substituted C3-C60 heteroaryl; R 11 Each is independently not connected to an adjacent ring structure; "*" represents the connection site; the expression of the ring structure with a "-" drawn through it indicates that the connection site is at any bond-forming position on the ring structure; R' and R'' are each independently selected from halogen, cyano, nitro, hydroxy, amino, C1-C20 linear alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of any one or at least two of them.

2. The boron and nitrogen-containing organic compound according to claim 1, wherein Ring E has a structure shown in Formula (c): Among them, the dotted line represents the fused bond of the group; Z 1 、Z 2 、Z 3 Each independently represents CR 12 or N; R 12 Each independently selected from at least one of hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C3-C60 heteroaryl; adjacent R 12 are not connected or are connected by a chemical bond to form a ring; R 12 each independently is not connected to the adjacent ring structure or is connected by a chemical bond to form a ring; Preferably, the Z 1 , Z 2 , Z 3 has at most one N.

3. The boron and nitrogen-containing organic compound according to claim 2, wherein The boron-nitrogen-containing organic compound has a structure shown in Formula (1-1): In formula (1-1), Z 1 , Z 2 , Z 3 have the same defined ranges as in formula (c); Ring A, Ring D, Ar1, Ar2, R a , R d have the same defined ranges as in formula (1); Preferably, in formula (1-1), the Z 1 , Z 2 , Z 3 at most one of them is N; Preferably, in formula (1-1), the Z 1 , Z 2 , Z 3 are each independently CR 12 .

4. The boron and nitrogen-containing organic compound according to claim 1 or 3, characterized in that, Ring A and Ring D have structures shown in Formula (d) or Formula (e): Among them, the dotted line represents the fused bond of the group; X is selected from O or S; U 1 、U 2 、U 3 、U 4 、U 5 、U 6 、U 7 、U 8 are each independently CR 13 or N; R 13 each independently selected from at least one of hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl; Adjacent R 13 are not connected or are connected by a chemical bond to form a ring; R 13 are each independently not connected to the adjacent ring structure or are connected by a chemical bond to form a ring; Preferably, the U 1 , U 2 , U 3 and U 4 has at most one N; the U 5 , U 6 , U 7 and U 8 has at most one N; Preferably, the U 1 , U 2 , U 3 and U 4 are each independently CR 13 ; the U 5 , U 6 , U 7 and U 8 are each independently CR 13 .

5. The boron and nitrogen-containing organic compound according to claim 4, wherein The boron-nitrogen-containing organic compound has a structure shown in Formula (3-1) or Formula (3-2): Among them, X has the same defined range as in Formula (e); U 1 、U 2 、U 3 、U 4 、U 5 、U 6 、U 7 、U 8 has the same defined ranges as in formula (d) and formula (e); U 1 ', U 2 ', U 3 ', U 4 ' have the same defined range as U 1 , U 2 , U 3 , U 4 ; Z 1 and Z 2 and Z 3 have the same defined ranges as in formula (c); Ar1 and Ar2 have the same defined range as in Formula (1).

6. The boron and nitrogen-containing organic compound according to claim 5, wherein Said Z 1 、Z 2 、Z 3 are each independently CR 12 ,U 1 、U 2 、U 3 、U 4 、U 5 、U 6 、U 7 、U 8 、U 1 '、U 2 '、U 3 '、U 4 ' are each independently CR 13 ; The R 12 , R 13 , Ar1, and Ar2, at least one of which is selected from the structures represented by Formula (2) or Formula (3); Preferably, at least one of Ar1 and Ar2 is selected from the structures shown in Formula (2) or Formula (3); Preferably, the at least one R 12 is selected from the structures represented by formula (2) or formula (3).

7. The boron and nitrogen-containing organic compound according to any one of claims 1-6, characterized in that In Formula (2) and Formula (3), the X1-X 12 are each independently CR 11 , R 11 are each independently selected from one of hydrogen, unsubstituted or R''-substituted C1-C20 linear alkyl, unsubstituted or R''-substituted C3-C20 cycloalkyl, unsubstituted or R''-substituted C6-C30 arylamino, unsubstituted or R''-substituted C3-C30 heteroarylamino, unsubstituted or R''-substituted C6-C60 aryl, and unsubstituted or R''-substituted C3-C60 heteroaryl. Preferably, at least one R 11 is selected from one of hydrogen, unsubstituted or R''-substituted C1-C20 linear alkyl, unsubstituted or R''-substituted C6-C60 aryl, and unsubstituted or R''-substituted C3-C60 heteroaryl; Each of said R” is independently selected from any one or a combination of at least two of halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, in Formula (2) and Formula (3), the X1-X 12 are each independently CR 11 , R 11 are each independently selected from one of hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl. Preferably, at least one R 11 is selected from one of hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl; Each of said R” is independently selected from a combination of one or two of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl; More preferably, in Formula (2) and Formula (3), the X1-X 12 are each independently CR 11 , and the R 11 are each independently selected from one of hydrogen, unsubstituted or R”-substituted C1-C10 linear alkyl, unsubstituted or R”-substituted C3-C10 cycloalkyl, unsubstituted or R”-substituted C6-C30 aryl, and unsubstituted or R”-substituted C3-C30 heteroaryl. Preferably, at least one R 11 is selected from one of hydrogen, unsubstituted or R”-substituted C1-C10 linear alkyl, unsubstituted or R”-substituted C6-C30 aryl, and unsubstituted or R”-substituted C3-C30 heteroaryl; Each of said R” is independently selected from a combination of one or two of C1-C6 linear alkyl, C6-C30 aryl, and C3-C30 heteroaryl.

8. The boron-nitrogen-containing organic compound according to claim 1 or 7, characterized in that, In Formula (2) and Formula (3), L1 is connected to X1 or X2; Preferably, in formula (2), X7 is CR 11 , wherein the R 11 is selected from one of hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl; each of the R”s is independently selected from one of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl; more preferably, in formula (2), X7 is CR 11 , wherein the R 11 is selected from one of hydrogen, C1-C20 linear alkyl, C6-C60 aryl, and C3-C60 heteroaryl, and X1 to X6, X8 to X 12 are each independently CR 11 , and the R 11 is selected from hydrogen; Preferably, in formula (3), X5, X6, X9, X 10 are each independently CR 11 , where R 11 is each independently selected from one of hydrogen, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl; each R” is independently selected from one of C1-C10 linear alkyl, C6-C30 arylamino, C6-C30 aryl, and C3-C30 heteroaryl; more preferably, in formula (3), X5, X6, X9, X 10 is CR 11 , where R 11 is each independently selected from one of hydrogen, C1-C20 linear alkyl, C6-C60 aryl, and C3-C60 heteroaryl; X1 to X4, X7 to X8, X 11 to X 12 are each independently CR 11 , and R 11 is selected from hydrogen.

9. The boron and nitrogen-containing organic compound according to any one of claims 4, 5 or 6, characterized in that, The R 12 , R 13 At least one of them is selected from the structures represented by Formula (2) or Formula (3), and the remaining R 12 , R 13 Are each independently selected from one or a combination of two of hydrogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, and C3-C60 heteroaryl; or R 12 , R 13 Are each independently selected from one or a combination of two of hydrogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the R 12 , R 13 At least one of them is selected from the structures shown in formula (2) or formula (3), and the remaining R 12 , R 13 Are each independently selected from one or a combination of two of hydrogen, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C20 arylamino, C6-C20 aryl, and C3-C20 heteroaryl; or R 12 , R 13 Are each independently selected from one or a combination of two of hydrogen, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C20 arylamino, C6-C20 aryl, and C3-C20 heteroaryl.

10. The boron-nitrogen-containing organic compound according to claim 1, wherein the compound has the structure shown below:

11. Use of the boron-nitrogen-containing organic compound according to any one of claims 1 to 10, wherein the use is as a functional material in an organic electronic device, and the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or an electronic paper; Preferably, the use of the organic compound is as a light-emitting layer material in an organic electroluminescent device, and more preferably as a light-emitting dye in the light-emitting layer.

12. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the boron-nitrogen-containing organic compound according to any one of claims 1 to 10; Preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the light-emitting layer contains the boron-nitrogen-containing organic compound according to any one of claims 1 to 10; Preferably, the light-emitting layer further includes a host material, and the host material has a structure shown by General Formula (a) or Formula (b): In formula (a) and formula (b), L 11 , L 12 each independently represents one of a single bond, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; Ar 11 、Ar 12 、Ar 21 、Ar 22 Each independently is one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; n represents any integer from 0 to 3; The above-mentioned substituted substituents are each independently any one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 linear alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, the host material has a structure shown by General Formula (a).

Images